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C5732

Sigma-Aldrich

CA-074

≥99% (TLC)

Synonym(e):

(L-3-trans-(Propylcarbamyl)oxirane-2-carbonyl)-L-isoleucyl-L-proline

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About This Item

Empirische Formel (Hill-System):
C18H29N3O6
CAS-Nummer:
134448-10-5
Molekulargewicht:
383.44
MDL-Nummer:
MFCD00797531
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24892580
NACRES:
NA.77

Biologische Quelle

synthetic (organic)

Qualitätsniveau

200

Assay

≥99% (TLC)

Form

powder

Löslichkeit

methanol: 1 mg/mL, clear, colorless

Lagertemp.

−20°C

SMILES String

CCCNC(=O)[C@H]1O[C@@H]1C(=O)N[C@@H]([C@H](C)CC)C(=O)N2CCC[C@H]2C(O)=O

InChI

1S/C18H29N3O6/c1-4-8-19-15(22)13-14(27-13)16(23)20-12(10(3)5-2)17(24)21-9-6-7-11(21)18(25)26/h10-14H,4-9H2,1-3H3,(H,19,22)(H,20,23)(H,25,26)/t10?,11-,12-,13-,14-/m0/s1

InChIKey

ZEZGJKSEBRELAS-NSIINPIOSA-N

Anwendung

CA-074 has been used as a cathepsin B inhibitor:
  • to study its effect on pseudotyped viruses bearing S proteins harboring R642M and N714K using HeLa cells
  • to determine the role of autophagy in glucose deprivation (GD)-induced damage
  • to study its effects on neuronal function upon exposure to His-cathepsin B (CATB)

Biochem./physiol. Wirkung

CA-074 is a potent and a selective inhibitor of cathepsin B. It is useful to study the biological function of cathepsin B in vivo. Studies show that CA-074 can also inhibit cathepsin L under reducing conditions.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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M Murata et al.
FEBS letters, 280(2), 307-310 (1991-03-25)
A series of new epoxysuccinyl peptides were designed and synthesized to develop a specific inhibitor of cathepsin B. Of these compounds, N-(L-3-trans-ethoxycarbonyloxirane-2-carbonyl)-L-isoleucyl-L-proli ne (compound CA-030) and N-(L-3-trans-propylcarbamoyloxirane-2-carbonyl)-L-isoleucyl-L-prol ine (compound CA-074) were the most potent and specific inhibitors of cathepsin B
Igor Stern et al.
The Biochemical journal, 381(Pt 2), 511-517 (2004-04-16)
The crystal structure of the inhibitor NS-134 in complex with bovine cathepsin B reveals that functional groups attached to both sides of the epoxysuccinyl reactive group bind to the part of active-site cleft as predicted. The -Leu-Pro-OH side binds to
Clément Naudin et al.
PloS one, 6(9), e25577-e25577 (2011-10-08)
Cysteine cathepsins have emerged as new players in inflammatory lung disorders. Their activities are dramatically increased in the sputum of cystic fibrosis (CF) patients, suggesting that they are involved in the pathophysiology of CF. We have characterized the cathepsins in
Eduardo Villalobo et al.
Eukaryotic cell, 2(6), 1234-1245 (2003-12-11)
The process of excystment of Sterkiella histriomuscorum (Ciliophora, Oxytrichidae) leads in a few hours, through a massive influx of water and the resorption of the cyst wall, from an undifferentiated resting cyst to a highly differentiated and dividing vegetative cell.
Arjen R de Boer et al.
Analytical chemistry, 77(24), 7894-7900 (2005-12-15)
The potential of high-temperature liquid chromatography (HTLC) was investigated in an on-line combination with a screening system for bioactive compounds against the enzyme cathepsin B. Samples were separated by HTLC and subsequently analyzed by an on-line continuous-flow enzymatic assay. Detection
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